Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:38 UTC
HMDB IDHMDB0014465
Secondary Accession Numbers
  • HMDB14465
Metabolite Identification
Common NameDihydroergotamine
DescriptionDihydroergotamine is only found in individuals that have used or taken this drug. It is a 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. [PubChem]Two theories have been proposed to explain the efficacy of 5-HT1D receptor agonists in migraine: 1) activation of 5-HT1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache and 2) activation of 5-HT1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.
Structure
Data?1582753183
Synonyms
ValueSource
5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotamanChEBI
9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trioneChEBI
9,10-DihydroergotamineChEBI
DihidroergotaminaChEBI
DihydroergotaminumChEBI
NeomigranKegg
9,10-Dihydro-ergotamineHMDB
Dihydroergotamine mesylateHMDB
Dihydroergotamine methanesulfonateHMDB
Dihydroergotamine monomethanesulfonateHMDB
ClavigreninHMDB
D Tamin retard l.u.t.HMDB
D.H.E. 45HMDB
DHE 45HMDB
DHE ratiopharmHMDB
Desitin brand OF dihydroergotamine mesylateHMDB
Methanesulfonate, dihydroergotamineHMDB
OrstanormHMDB
Shire brand OF dihydroergotamine mesylateHMDB
Wernigeroide brand OF dihydroergotamine mesylateHMDB
Alpharma brand OF dihydroergotamine mesylateHMDB
AngionormHMDB
Anto brand OF dihydroergotamine mesylateHMDB
DHE-purenHMDB
Dihydroergotamine-sandozHMDB
ErgomimetHMDB
IPRAD brand OF dihydroergotamine mesylateHMDB
IkaranHMDB
MigranalHMDB
Pierre fabre brand OF dihydroergotamine mesylateHMDB
SeglorHMDB
Xcel brand 2 OF dihydroergotamine mesylateHMDB
CT Arzneimittel brand OF dihydroergotamine mesylateHMDB
CT-Arzneimittel brand OF dihydroergotamine mesylateHMDB
AgitHMDB
DET MSHMDB
DHE purenHMDB
DHE-ratiopharmHMDB
DHE45HMDB
Dihydroergotamin alHMDB
DihytaminHMDB
ErgantonHMDB
Farmasan brand OF dihydroergotamine mesylateHMDB
Q-Pharm brand OF dihydroergotamine mesylateHMDB
TamikHMDB
Verla brand OF dihydroergotamine mesylateHMDB
Xcel brand 1 OF dihydroergotamine mesylateHMDB
Ergotam von CTHMDB
Aliud brand OF dihydroergotamine mesylateHMDB
D-Tamin retard l.u.t.HMDB
DHE-45HMDB
DihydergotHMDB
Dihydroergotamine sandozHMDB
ErgontHMDB
Fujisawa brand OF dihydroergotamine mesylateHMDB
Hormosan brand OF dihydroergotamine mesylateHMDB
Mesylate, dihydroergotamineHMDB
Novartis brand OF dihydroergotamine mesylateHMDB
Pharmafrid brand OF dihydroergotamine mesylateHMDB
Q Pharm brand OF dihydroergotamine mesylateHMDB
Sanol brand OF dihydroergotamine mesylateHMDB
Schwarz brand OF dihydroergotamine mesylateHMDB
VerladynHMDB
Ratiopharm brand OF dihydroergotamine mesylateHMDB
Von CT, ergotamHMDB
Chemical FormulaC33H37N5O5
Average Molecular Weight583.6774
Monoisotopic Molecular Weight583.279469319
IUPAC Name(2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
Traditional Namedihydroergotamine
CAS Registry Number6190-39-2
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)O[C@@]21O
InChI Identifier
InChI=1S/C33H37N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
InChI KeyLUZRJRNZXALNLM-JGRZULCMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentErgotamines, dihydroergotamines, and derivatives
Alternative Parents
Substituents
  • Dihydroergotamine
  • Ergotamine
  • Hybrid peptide
  • Alpha-dipeptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • N-acyl-alpha amino acid or derivatives
  • Pyrroloquinoline
  • Alpha-amino acid or derivatives
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Piperidinecarboxamide
  • 3-piperidinecarboxamide
  • Aralkylamine
  • N-alkylpiperazine
  • Benzenoid
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Oxazolidinone
  • Piperazine
  • Piperidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Oxazolidine
  • Pyrrolidine
  • Pyrrole
  • Amino acid or derivatives
  • Lactam
  • Tertiary aliphatic amine
  • Secondary carboxylic acid amide
  • Orthocarboxylic acid derivative
  • Carboxamide group
  • Tertiary amine
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Alkanolamine
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP3.04ALOGPS
logP2.71ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.71ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity159.39 m³·mol⁻¹ChemAxon
Polarizability63.3 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-256.82430932474
DeepCCS[M+Na]+230.64730932474
AllCCS[M+H]+235.032859911
AllCCS[M+H-H2O]+234.032859911
AllCCS[M+NH4]+235.932859911
AllCCS[M+Na]+236.132859911
AllCCS[M-H]-214.132859911
AllCCS[M+Na-2H]-216.132859911
AllCCS[M+HCOO]-218.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydroergotamine[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)O[C@@]21O5467.4Standard polar33892256
Dihydroergotamine[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)O[C@@]21O4311.6Standard non polar33892256
Dihydroergotamine[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)O[C@@]21O5400.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroergotamine,1TMS,isomer #1CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214713.4Semi standard non polar33892256
Dihydroergotamine,1TMS,isomer #2CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214614.2Semi standard non polar33892256
Dihydroergotamine,1TMS,isomer #3CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214701.2Semi standard non polar33892256
Dihydroergotamine,2TMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214624.3Semi standard non polar33892256
Dihydroergotamine,2TMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214804.3Standard non polar33892256
Dihydroergotamine,2TMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]216065.9Standard polar33892256
Dihydroergotamine,2TMS,isomer #2CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214666.8Semi standard non polar33892256
Dihydroergotamine,2TMS,isomer #2CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214728.0Standard non polar33892256
Dihydroergotamine,2TMS,isomer #2CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]216064.5Standard polar33892256
Dihydroergotamine,2TMS,isomer #3CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214589.6Semi standard non polar33892256
Dihydroergotamine,2TMS,isomer #3CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214721.6Standard non polar33892256
Dihydroergotamine,2TMS,isomer #3CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]216078.6Standard polar33892256
Dihydroergotamine,3TMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214611.1Semi standard non polar33892256
Dihydroergotamine,3TMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]214729.3Standard non polar33892256
Dihydroergotamine,3TMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]215821.5Standard polar33892256
Dihydroergotamine,1TBDMS,isomer #1CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214908.4Semi standard non polar33892256
Dihydroergotamine,1TBDMS,isomer #2CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214815.5Semi standard non polar33892256
Dihydroergotamine,1TBDMS,isomer #3CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]214880.9Semi standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]214990.7Semi standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]215241.0Standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #1CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]216092.5Standard polar33892256
Dihydroergotamine,2TBDMS,isomer #2CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]215034.9Semi standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #2CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]215143.9Standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #2CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]216112.5Standard polar33892256
Dihydroergotamine,2TBDMS,isomer #3CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]214963.9Semi standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #3CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]215120.3Standard non polar33892256
Dihydroergotamine,2TBDMS,isomer #3CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]216128.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fr5-5891210000-f53c38352e2598f9007e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (1 TMS) - 70eV, Positivesplash10-0fdn-7491022000-6c73d0337e04ab2f69182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS ("Dihydroergotamine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroergotamine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Positive-QTOFsplash10-001i-0022090000-bfd200952b03e8b137ff2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Positive-QTOFsplash10-0un9-0091010000-c5661ba02ab58100d0462016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Positive-QTOFsplash10-004i-4590000000-dc4a0cca36e4ae6c18c52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Negative-QTOFsplash10-0019-0049160000-4fdc70b6d84db2eb175e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Negative-QTOFsplash10-03xr-2196220000-3c3fcf127102792f663c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Negative-QTOFsplash10-0g4j-9810000000-88f13186254d2bf07e892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Positive-QTOFsplash10-001i-0000090000-3abf973bfa14967f7f1d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Positive-QTOFsplash10-001i-0010290000-1037c6e147fa5f93e6532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Positive-QTOFsplash10-004i-0090010000-f5347f35594f87c4297f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Negative-QTOFsplash10-001i-0000090000-10b01aae8e192c05edc62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Negative-QTOFsplash10-001i-2100390000-475a2b73d09ae5f9c1742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Negative-QTOFsplash10-0v03-9351430000-9c41d997e0687489c4ee2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00320 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00320 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00320
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001724
Chemspider ID10091
KEGG Compound IDC07798
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydroergotamine
METLIN IDNot Available
PubChem Compound10531
PDB IDNot Available
ChEBI ID4562
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Schaerlinger B, Hickel P, Etienne N, Guesnier L, Maroteaux L: Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy. Br J Pharmacol. 2003 Sep;140(2):277-84. Epub 2003 Aug 11. [PubMed:12970106 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
References
  1. Willems EW, Trion M, De Vries P, Heiligers JP, Villalon CM, Saxena PR: Pharmacological evidence that alpha1-and alpha2-adrenoceptors mediate vasoconstriction of carotid arteriovenous anastomoses in anaesthetized pigs. Br J Pharmacol. 1999 Jul;127(5):1263-71. [PubMed:10455274 ]
  2. Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]
  3. Buzzi MG, Moskowitz MA: Evidence for 5-HT1B/1D receptors mediating the antimigraine effect of sumatriptan and dihydroergotamine. Cephalalgia. 1991 Sep;11(4):165-8. [PubMed:1660351 ]
  4. Yu XJ, Waeber C, Castanon N, Scearce K, Hen R, Macor JE, Chauveau J, Moskowitz MA: 5-Carboxamido-tryptamine, CP-122,288 and dihydroergotamine but not sumatriptan, CP-93,129, and serotonin-5-O-carboxymethyl-glycyl -tyrosinamide block dural plasma protein extravasation in knockout mice that lack 5-hydroxytryptamine1B receptors. Mol Pharmacol. 1996 May;49(5):761-5. [PubMed:8622623 ]
  5. Pauwels PJ, Palmier C, Dupuis DS, Colpaert FC: Interaction of 5-HT1B/D ligands with recombinant h 5-HT1A receptors: intrinsic activity and modulation by G-protein activation state. Naunyn Schmiedebergs Arch Pharmacol. 1998 May;357(5):490-9. [PubMed:9650800 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular weight:
41906.4
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Lesage AS, Wouters R, Van Gompel P, Heylen L, Vanhoenacker P, Haegeman G, Luyten WH, Leysen JE: Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65. [PubMed:9605573 ]
  3. Buzzi MG, Moskowitz MA: The trigemino-vascular system and migraine. Pathol Biol (Paris). 1992 Apr;40(4):313-7. [PubMed:1379707 ]
  4. Buzzi MG, Dimitriadou V, Theoharides TC, Moskowitz MA: 5-Hydroxytryptamine receptor agonists for the abortive treatment of vascular headaches block mast cell, endothelial and platelet activation within the rat dura mater after trigeminal stimulation. Brain Res. 1992 Jun 26;583(1-2):137-49. [PubMed:1324091 ]
  5. Silberstein SD, McCrory DC: Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache. 2003 Feb;43(2):144-66. [PubMed:12558771 ]
  6. Hoyer D, Lery H, Waeber C, Bruinvels AT, Nozulak J, Palacios JM: "5-HT1R" or 5-HT1D sites? Evidence for 5-HT1D binding sites in rabbit brain. Naunyn Schmiedebergs Arch Pharmacol. 1992 Sep;346(3):249-54. [PubMed:1407010 ]
  7. Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
  2. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]